6-iodovanillamine | 859172-19-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 6-iodovanillamine
• 英文别名: 4-(Aminomethyl)-5-iodo-2-methoxyphenol
• CAS: 859172-19-3
• 化学式: C₈H₁₀INO₂
• 分子量: 279.077
• InChiKey: ROBSFPSNQJNQKB-UHFFFAOYSA-N

物化性质

• 沸点：
  377.1±42.0 °C(Predicted)
• 密度：
  1.813±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  55.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-iodovanillamine 、 维A酸 在 1-丙基磷酸酐 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以49%的产率得到N-(4-hydroxy-6-iodo-3-methoxybenzyl)retinamide
  参考文献：
  名称：

  The Taming of Capsaicin. Reversal of the Vanilloid Activity of N-Acylvanillamines by Aromatic Iodination

  摘要：

  Aromatic iodination ortho to the phenolic hydroxyl reverts the activity of the ultrapotent vanilloid agonist resiniferatoxin (RTX, 1a), generating the ultrapotent antagonist 5'-iodoRTX (1b). To better understand the role of iodine in this remarkable switch of activity, a systematic investigation on the halogenation of vanillamides, a class of compounds structurally simpler than resiniferonoids, was carried out. The results showed that (a) the antagonistic activity depends on the site of halogenation and is maximal at C-6', (b) iodine is more efficient than chlorine and bromine at reverting the agonistic activity, and (c) iodine-carbon exchange decreases antagonist activity. Iodine-induced reversal of vanilloid activity was also observed in vanillamides more powerful than capsaicin, but a poor correlation was found between agonistic and antagonistic potencies, suggesting that differences exist in the way vanillamides and their 6'-iodo derivatives bind to TRPV1".

  DOI：

  10.1021/jm050139q
• 作为产物：
  描述：

  3-methoxy-4-<2'-(methoxyethoxy)methoxy>-benzaldehyde 在 锌 sodium tetrahydroborate 、 二苯基磷酸 、 氢溴酸 、 碘 、 silver trifluoroacetate 、 氯化铵 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 甲苯 为溶剂， 反应 9.0h， 生成 6-iodovanillamine
  参考文献：
  名称：

  The Taming of Capsaicin. Reversal of the Vanilloid Activity of N-Acylvanillamines by Aromatic Iodination

  摘要：

  Aromatic iodination ortho to the phenolic hydroxyl reverts the activity of the ultrapotent vanilloid agonist resiniferatoxin (RTX, 1a), generating the ultrapotent antagonist 5'-iodoRTX (1b). To better understand the role of iodine in this remarkable switch of activity, a systematic investigation on the halogenation of vanillamides, a class of compounds structurally simpler than resiniferonoids, was carried out. The results showed that (a) the antagonistic activity depends on the site of halogenation and is maximal at C-6', (b) iodine is more efficient than chlorine and bromine at reverting the agonistic activity, and (c) iodine-carbon exchange decreases antagonist activity. Iodine-induced reversal of vanilloid activity was also observed in vanillamides more powerful than capsaicin, but a poor correlation was found between agonistic and antagonistic potencies, suggesting that differences exist in the way vanillamides and their 6'-iodo derivatives bind to TRPV1".

  DOI：

  10.1021/jm050139q

文献信息

• VANILLOID TRPV1 RECEPTOR ANTAGONISTS
  申请人：BARALDI Pier Giovanni

  公开号：US20080085936A1

  公开（公告）日：2008-04-10

  The invention relates to compounds of formula (I), wherein R, R 1 , R 2 , X and n are as defined in the description, and their use for the preparation of pharmaceutical compositions for the treatment of inflammatory states.

  本发明涉及式(I)的化合物，其中R、R1、R2、X和n如所述定义，以及它们的用途，用于制备治疗炎症状态的药物组合物。
• US7964642B2
  申请人：——

  公开号：US7964642B2

  公开（公告）日：2011-06-21